A/N I realized it takes longer doing individual imagines so I'm just going to put them together. Don't worry I'll still do single ones.
PONYBOY: After track practice you stayed a little later after hitting the showers. You were stopped by the sunset. You just stood there admiring everything until you felt a soft hand on your shoulder. It was Ponyboy.
"You like sunsets too?" He asked with a small smile. "Yeah, I watch them every chance I get," you were still looking until the colors started to fade. "And then that's the end of the story. See you tomorrow Pony."
You and Ponyboy have grown a friendship for the past months. What you didn't know was Pony had feelings for you.
"Hey (Y/N) wait up, I need to ask you something." He caught up and grabbed your hand making you blush furiously. "What's up?"
"I was kind of wondering if you'd go out w-with me." You didn't know what to do at that point so you threw yourself into a hug feeling Ponyboy hug you back. "So is that a yes," Ponyboy asked between a chuckle. "Of course." You answered hugging tighter.
JOHNNY: Ever since you've gotten jumped, Johnny has always been by your side. You two have gotten so close you started to catch feelings. You really wanted it to become something more.
"Johnny can I talk to you about something." You looked down. "What's up (Y/N)?"
"We've gotten really close ever since my... incident and I-I kind of have.." you were interrupted by Johnny. "(Y/N) will you go out with me?
You stood there kind of shock then happiness took over.
STEVE: You and (Y/BF/N) have probably been in Tulsa for about a 2 to 4 months and you loved it besides that fact that you have been hanging out with Steve since then. It wasn't hard to see you two had feeling just never made it more.
Steve might seem like the guy to ask you out no sweat but actually he was shy in this type of situation.
You woke up, did your daily routine then went to work. You had gotten a job at the Dingo. Like you always did you talked to the drunk stranger that always is there. He loved Mickey Mouse, that's all ever he talked about.
When you got to the back there was a rose with a note. S.R. You smiled at his sloppy hand writing. "Hey (Y/N), I know I can't be up front with you but I really like you and I was wonder if you would like to go on a date." You were so happy you started dancing until your boss came in.
"(Y/N)... I'll let the boy know you said yes."
DALLY: Dally. Dally. Dally. That's all you been thinking about. You'd thought you didn't want him but there's just something about him.
You were in Shepard's gang, mostly because you were Tim's baby sister. Your brother didn't really like Dallas too much so you had to stay away.
You usually walk around terrorizing any Soc you saw but you decided to play it cool and pay Dally a visit. When you went to knock on the door Dally came bursting out making you fall under him.
"Get off of me Winston." You pushed him off blushing. Dallas got up staring at you.
"(Y/N) I know we haven't known each other long enough but wanna go out sometime?" Right when you were going to answer Tim shouted out for you. "Text me with details."
You ran off smiling like a dummy.